Director of Sales - East Region

About Sweed

Sweed is a product-driven SaaS company on a mission to “shatter the myth that cannabis software is always the best of the worst” by giving retailers an all-in-one platform that combines POS, payments, e-commerce, marketing, analytics and inventory management. Founded in 2018, the team of ~200 operates remotely across the US and internationally, serving single-store operators through multi-state enterprises with compliant, automation-first tools.

Role Summary

As Director of Sales, East Region, you will lead a team of high-performing Account Executives and Field Marketing Reps to exceed monthly door-count, lead generation, and ARR targets across your assigned region. You’ll be responsible for coaching execution, pipeline accountability, and regional coordination ensuring every rep hits quota and every market gets stronger.

Key Responsibilities

Regional Leadership & Coaching

• Directly manage and develop 4 AEs and 5 FMRs in the East Region.

• Conduct weekly forecast and pipeline reviews with each team member.

• Team accountability to HubSpot pipeline hygiene, lead routing, and activity tracking.

• Uphold Sweed’s coaching culture: inspect what you expect, praise progress, and hold firm on outcomes.

Revenue Execution

• Hit or exceed monthly new door targets and ARR goals aligned with Sweed’s 2025 plan.

• Analyze conversion funnels and launch experiments to improve demo-to-close rate, average ACV, and time-to-live metrics.

• Monitor quota attainment weekly and intervene early with underperformers.

GTM Cadence & Territory Design

• Prioritize coverage across tiered market opportunities (license velocity, market maturity, local events).

• Allocate AE/FMR resources accordingly and refine territories quarterly.

• Collaborate with Field Marketing, Product, and Customer Success to execute campaigns, pilots, and new market launches.

Field & Partner Enablement

• Ensure reps are effectively using Sweed's event programs, partner referrals, and local campaigns.

• Review contact-to-demo conversion rates and event ROI monthly.

• Share competitive intel and customer feedback to influence product roadmap and pricing strategy.

Required Qualifications

• 5+ years managing quota-carrying SaaS sales teams (B2B)

• Strong leadership track record in regional or territory-based sales roles

• Experience hiring, training, and coaching AEs and/or field teams

• CRM mastery (HubSpot preferred); disciplined in forecast and pipeline rigor

• Cannabis, POS, or payments industry experience highly preferred

• Able to travel 50%+ across the East Coast for team support and events

Preferred Qualifications

• Experience building GTM playbooks (AE/FMR model)

• Familiarity with startup-stage SaaS operations and metrics (0 → $50M ARR)

• Background working with partner-led and event-led lead gen programs

• Comfortable operating in dynamic, compliance-heavy environments

Compensation & Benefits

• Competitive base + variable structure tied to regional door and ARR targets

• Remote-first flexibility and company-sponsored travel.

• Health, dental, vision, life, and short term disability insurance.

• Generous PTO, holidays, and remote-first flexibility

Originally posted on Himalayas